2-(Bromomethyl)tetrahydro-2H-pyran → 7'-(trifluoromethyl)-1'-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one
Reaktionsgleichung
Br[CH2:2][C:3]1[O:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][CH:4]=1.BrCC1CCCCO1.[F:20][C:21]([F:44])([F:43])[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:30]=1[NH:29][C:28](=[O:31])[C:27]12[C:35]2=[CH:36][C:37]3[O:41][CH2:40][O:39][C:38]=3[CH:42]=[C:34]2[O:33][CH2:32]1>>[F:44][C:21]([F:20])([F:43])[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:30]=1[N:29]([CH2:2][C:3]1[O:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][CH:4]=1)[C:28](=[O:31])[C:27]12[C:35]2=[CH:36][C:37]3[O:41][CH2:40][O:39][C:38]=3[CH:42]=[C:34]2[O:33][CH2:32]1Komponenten
4
Edukt 3
Produkt 1
Versuchsvorschrift
Following the procedure as described in EXAMPLE 4 and making non-critical variations using 5-bromomethyl-2-(trifluoromethyl)furan to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 7′-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 7′-(trifluoromethyl)-1′-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one was obtained (43%) as a colorless solid: mp 95-98° C.; 1H NMR (300 MHz, CDCl3) δ7.59 (d, J=8.1 Hz, 1H), 7.36 (d, J=7.3 Hz, 1H), 7.15 (dd, J=7.8, 7.8 Hz, 1H), 6.69 (d, J=3.2 Hz, 1H), 6.50 (s, 1H), 6.23 (d, J=3.0 Hz, 1H), 6.10 (s, 1H), 5.86 (d, J=3.0 Hz, 2H), 5.23 (ABq, 2H), 4.78 (ABq, 2H); 13C NMR (75 MHz, CDCl3) δ178.6, 156.0, 152.2, 149.3, 142.7, 141.4 (q), 139.1, 135.1, 127.9, 127.0 (m), 122.9 (d), 121.1 (d), 119.3 (d), 118.7, 113.4 (q), 112.5, 108.2, 102.8, 101.7, 93.7, 80.8, 56.9, 39.4; MS (ES+) m/z 498.4 (M+1).